EP1854783B1 - Verfahren zur Herstellung von Isocyanaten - Google Patents
Verfahren zur Herstellung von Isocyanaten Download PDFInfo
- Publication number
- EP1854783B1 EP1854783B1 EP07008910.7A EP07008910A EP1854783B1 EP 1854783 B1 EP1854783 B1 EP 1854783B1 EP 07008910 A EP07008910 A EP 07008910A EP 1854783 B1 EP1854783 B1 EP 1854783B1
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- EP
- European Patent Office
- Prior art keywords
- solvent
- phosgene
- stream
- solution
- mdi
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000012948 isocyanate Substances 0.000 title description 13
- 150000002513 isocyanates Chemical class 0.000 title description 13
- 239000002904 solvent Substances 0.000 claims description 115
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 92
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 57
- 150000001412 amines Chemical class 0.000 claims description 38
- 238000004821 distillation Methods 0.000 claims description 30
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000005442 diisocyanate group Chemical group 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 8
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 239000000243 solution Substances 0.000 description 60
- 239000000203 mixture Substances 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 17
- 238000000746 purification Methods 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 229920000768 polyamine Polymers 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000012045 crude solution Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000007700 distillative separation Methods 0.000 description 3
- -1 polyphenylene Polymers 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical class CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 description 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- CGYGETOMCSJHJU-UHFFFAOYSA-N 2-chloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC=C21 CGYGETOMCSJHJU-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
Definitions
- the invention relates to a process for the preparation of di- and polyisocyanates of the diphenylmethane series (MDI), by reaction of the corresponding amines dissolved in a solvent with phosgene, subsequent separation of hydrogen chloride and excess phosgene, followed by distillative separation of the MDI-containing crude solution thus obtained in MDI and solvents, recycling of the solvent and preparation of solutions of amines and phosgene, wherein the proportion of the solvent used to prepare the solution of amines, low levels of phosgene and diisocyanates of the diphenylmethane series identifies.
- MDI diphenylmethane series
- DE-A-19942299 describes a process for the preparation of mono- and oligoisocyanates by phosgenation of the corresponding amines, wherein a catalytic amount of a monoisocyanate is presented in an inert solvent with phosgene, the amine, usually dissolved in solvent, is added and the resulting reaction mixture is reacted with phosgene.
- the process is, especially by using the additional monoisocyanate, which later has to be separated again, relatively complicated. A lesson for the required purity of the solvent is not apparent.
- EP-A-1 073 628 describes a process for the preparation of mixtures of diphenylmethane diisocyanates and polyphenyl-polymethylene-polyisocyanates (so-called polymeric MDI) by two-stage reaction of the mixture of the corresponding amines with phosgene in the presence of a solvent while maintaining selected ratios of phosgene and hydrogen chloride in the second process stage. After the two-step reaction of the amine with phosgene in the selected solvent, the excess phosgene, hydrogen chloride and solvent are separated from the reaction product (MDI) by distillation.
- MDI reaction product
- EP-A-1 073 628 point out that it is advantageous for a good product quality that the residual content of phosgene in the Reaction solution after phosgene removal ⁇ 10 ppm. A lesson for the required purity of the circulation solvent is also not apparent.
- WO 99/542 89 describes a process for preparing mixtures of diphenylmethane diisocyanates and polyphenylene polymethylene polyisocyanates.
- the solvent recovered in the work-up and separation of the crude MDI solution contains several hundred ppm of free phosgene, based on the weight of the solvent. This is even the case even if the crude MDI solution is previously freed from phosgene so far that no free phosgene is detectable. Hence, therefore, phosgene is formed or split off from secondary components in the work-up.
- Suitable organic amines are 4,4'-, 2,4'- or 2,2'-diphenylmethanediamine or mixtures thereof, as well as higher molecular weight isomeric, oligomeric or polymeric derivatives of said amines.
- Amines for the process according to the invention are therefore the di- and polyamines of the diphenylmethane series (MDA, monomeric, oligomeric and polymeric amines).
- MDA diphenylmethane series
- MDI diphenylmethane series
- Suitable solvents for use in the process according to the invention are, for example, chlorinated aromatic hydrocarbons, such as chlorobenzene, o-dichlorobenzene, p-dichlorobenzene, trichlorobenzenes, the corresponding chlorotoluenes or chloroxylenes, chloroethylbenzene, monochlorodiphenyl, ⁇ - or ⁇ -naphthyl chloride, ethyl benzoate, dialkyl phthalate , Diisodiethylphthalat, toluene and xylenes and methylene chloride, perchlorethylene, trichlorofluoromethane and / or butyl acetate. Mixtures of these exemplified solvents can also be used. Other examples of suitable solvents are known in the art.
- the sensible heat of the recovered solvent stream is wholly or partly used as the energy source for this Abtreimungs Republic. This can be done, for example, by heating the feed into the distillation column via a heat exchanger to the bottom of the column.
- a suitable variant of this embodiment of the method according to the invention is in FIG. 3 shown. Since normally the distillatively separated solvent is obtained at a temperature of> 100 ° C, which should have to generate the solution of amine in the solvent, however, for optimal Phosgenier discipline ⁇ 50 ° C, so the separation of the residual amounts of phosgene simultaneously with a cooling of the Solvent be connected.
- the stream containing MDI contains at least 95% by weight of MDI. based on the weight of the MDI-containing stream.
- the solvent-containing stream contains at least 95% by weight of solvent, based on the weight of the solvent-containing stream.
- Fig. 1 the process according to the invention for the preparation of isocyanates is shown schematically by way of example.
- step 1 level 1, the Vorphosgenierscale (mixer 1) and level 2, the H regardingphosgenierwriting (phosgenation reactor 2).
- Steps 1 and 2 correspond to step b) of the process according to the invention.
- stage 3 dephosgenation stage 3
- hydrogen chloride and excess phosgene are separated from the reaction solution containing MDI (step c)).
- step c technically preferably a large part of the hydrogen chloride formed, together with the excess phosgene, is already separated off directly at the exit from the phosgenation reactor 2, another part in a dephosgenation column.
- stage 4 distillation stage 4
- step d distillation stage 4
- step 6 solvent purification 6
- step 5 vapor column 5
- step 5 vapor column 5
- the work-up of the vapors obtained in stages 2 and 3 takes place (in the main, recovery of phosgene and proportionate amount of solvent).
- the solution of phosgene in the solvent (phosgene solution) is prepared.
- the solution of amine in the solvent (amine solution) is prepared from the amine (stream 8) and the recycled solvent stream (stream 21) largely freed from MDI and phosgene.
- one of the solutions can be prepared at least proportionally with fresh solvent.
- the phosgene solution and the amine solution are reacted in the mixer 1 with intensive mixing and the resulting mixture (stream 9) in the Phosgenierreaktor 2 by heating with elimination of hydrogen chloride in the MDI containing reaction solution (stream 10) implemented.
- distillation stage 4 the crude MDI solution (stream 11) is separated by distillation into MDI (MDI-containing stream 12) and the recovered solvent (solvent-containing stream 17). Since MDI usually has a higher boiling point than the solvent has, by suitable design of the workup in the distillation stage 4 can be ensured that the solvent (solvent-containing stream 17) the required low diisocyanate content of ⁇ 100 ppm, preferably ⁇ 50 ppm, more preferably ⁇ 20 ppm, based on the weight of the solvent containing stream.
- the solvent-containing stream (stream 17) since phosgene is split off from secondary components of the phosgenation in the workup in the distillation stage 4, the solvent-containing stream (stream 17) always has a residual content of phosgene. This is now separated in the solvent purification 6 as a phosgene-enriched solvent stream (stream 18) and can be returned to the process and, for example, added to the stream 16 (not shown in FIG. 1 ).
- the purified solvent-containing stream 19 having a phosgene content of ⁇ 100 ppm, preferably ⁇ 50 ppm, more preferably ⁇ 20 ppm, and a diisocyanate content of ⁇ 100 ppm, preferably ⁇ 50 ppm, more preferably ⁇ 20 ppm, each based on the weight of Solvent-containing stream can be partially discharged as stream 20 and used elsewhere in the process, but is at least partially, preferably used predominantly as stream 21 for the preparation of the amine solution.
- reaction of the amine solution with the Phösgen regards in step b) is usually carried out at temperatures of 20 to 240 ° C and absolute pressures of 1 to 50 bar. It can be carried out in one or more stages, with phosgene usually being used in stoichiometric excess.
- the amine solution and the phosgene solution are preferably combined via static mixing elements or special dynamic mixing elements and then passed in step 2, for example from bottom to top through one or more reaction towers in which the mixture reacts to MDI.
- reaction vessels with stirring device can also be used. Suitable static and dynamic mixing elements and reaction devices are known from the prior art.
- step c) The separation of residual phosgene and hydrogen chloride in step c) from the resulting MDI-containing reaction solution is advantageously carried out in the Entphosgeniertreatment 3, wherein the MDI-containing reaction solution is added to the stripping section of a distillation column.
- this distillation step is carried out so that the entphosgenated MDI crude solution is obtained as the bottom product with a residual content of phosgene of ⁇ 100 ppm, preferably ⁇ 10 ppm, based on the weight of the crude isocyanate solution.
- the distillative separation of the crude MDI solution in step d) is carried out in a manner adapted to the boiling point of the solvent in a one- or preferably multi-stage distillation sequence in the distillation stage 4.
- Such distillation sequences are known from the prior art.
- this distillative separation in step d) can advantageously be carried out such that the crude isocyanate solution in two steps in a bottom product containing at least 95 wt .-%, particularly preferably at least 97 wt .-% of MDI, based on the weight of the MDI-containing stream, worked up, which is then preferably freed in further steps of low boilers.
- the first step 60-90% of the solvent contained in the crude MDI solution is preferably separated off by flash distillation at absolute pressures of 600-1200 mbar and bottom temperatures of 110-170 ° C., the vapors being separated in a distillation column having 5-20 separation stages and 10 - 30% reflux are worked up so that a solvent-containing stream having a diisocyanate content of ⁇ 100 ppm, preferably ⁇ 50 ppm, more preferably ⁇ 20 ppm, based on the weight of the solvent-containing stream is achieved.
- the residual solvent is separated off to a residual content of 1-3% by weight in the bottom product at absolute pressures of 60-140 mbar and bottom temperatures of 130-190 ° C.
- the vapors can also be worked up in a distillation column with 5 to 20 stages and 10 to 40% reflux, so that a solvent-containing stream having a diisocyanate content of ⁇ 100 ppm, preferably ⁇ 50 ppm, more preferably ⁇ 20 ppm, by weight the solvent-containing stream, is achieved or recycled after recondensation as feed in the first distillation step.
- a solvent-containing stream having a diisocyanate content of ⁇ 100 ppm, preferably ⁇ 50 ppm, more preferably ⁇ 20 ppm, by weight the solvent-containing stream is achieved or recycled after recondensation as feed in the first distillation step.
- the distillate streams separated off in the following steps can be recycled as feed to the first distillation step.
- Diisocyanate ( ⁇ 100 ppm of diisocyanates, based on the weight of the solvent-containing stream) are separated in an advantageous manner.
- this stream containing solvent may contain as impurity monoisocyanates (eg phenyl isocyanate) with a content of 100-1000 ppm and a residual phosgene amount of 100-1000 ppm.
- this distillation is carried out only after the diisocyanate content to be achieved of ⁇ 100 ppm, preferably ⁇ 50 ppm,
- the solvent purification comprises a stripping column 31, a bottom evaporator 32 and a top condenser 33.
- the stream 17 containing the weakly phosgene - containing solvent from the workup in stage 4 (not shown in FIG. 2 ) is applied to the stripping column 31, which preferably has 4 to 20 separation stages.
- the sump evaporator 32 generates by heating eg with heating steam sufficient amounts of vapors, so that the dephosgenated solvent-containing stream 19 only a phosgene content of ⁇ 100 ppm, preferably ⁇ 50 ppm, more preferably ⁇ 20 ppm, and a diisocyanate content of ⁇ 100 ppm, preferably ⁇ 50 ppm, particularly preferably ⁇ 20 ppm, in each case based on the weight of the solvent-containing stream, and can thus be used for the preparation of the amine solution.
- the generated vapor stream 36 contains the separated phosgene in preferably 1-6 wt .-%, based on the weight of the vapor stream, and is preferably condensed on the condenser 33; while the condensate 37 is fed into the isocyanate process, for example for the preparation of the phosgene solution, the residual gases 38 are preferably fed to the exhaust gas treatment.
- the condensate 37 can also be wholly or partially recycled as reflux to the stripping column 31, whereby the phosgene further concentrated in the vapor stream 36. If the stage 6 is operated at a pressure below the boiling temperature of the solvent in the solvent-containing stream 17, a partial separation of phosgene already occurs when it enters the stripping column 31 by flashing. Thus, the amount of energy to be supplied to the evaporator 32 is reduced.
- Fig. 3 finally shows a particularly preferred, because energetically particularly favorable embodiment of the distillative solvent purification in step 6:
- the weakly phosgene-containing solvent stream 17 from the workup in step 4 (not shown in FIG. 3 ) is first applied as a heating medium through the bottom evaporator 32 and then to the stripping column 31, which has 4 to 20 separation stages.
- the bottom evaporator 32 generates by heating with the solvent-containing stream sufficient amounts of vapors, so that the dephosgenated solvent-containing stream 19 only a phosgene content of ⁇ 100 ppm, preferably ⁇ 50 ppm, more preferably ⁇ 20 ppm, and a diisocyanate content of ⁇ 100 ppm, preferably ⁇ 50 ppm, more preferably ⁇ 20 ppm, each based on the weight of the solvent-containing stream, and thus can be used to prepare the amine solution.
- the solvent stream is cooled by 2 - 10 ° C.
- the generated vapor stream 36 contains the separated phosgene in preferably 1-6 wt .-%, based on the weight of the vapor stream, and is preferably condensed on the condenser 33; While the condensate 37 is fed into the MDI process, for example for the preparation of the phosgene solution, the residual gases 38 are preferably fed to the exhaust gas treatment via a vacuum system. However, the condensate 37 can also be wholly or partially recycled as reflux to the stripping column 31, whereby the phosgene further concentrated in the vapor stream 36. By controlling the pressure in the system, the amount of generated vapors and thereby the quality or purity of the solvent-containing stream is regulated. Overall, in this embodiment, the separation of the residual amounts of phosgene is effected without supply of external energy, while at the same time causing a normally desirable cooling of the solvent-containing stream used to prepare the amine solution.
- the mixture is then cooled to 100 ° C, expanded to atmospheric pressure and neutralized by addition of 54 g of 50 wt.% Aqueous sodium hydroxide solution with stirring. After switching off the stirrer, the phases are allowed to settle and the lower aqueous phase is sucked off. Excess aniline is then first distilled off under atmospheric pressure with residual water remaining and the aniline residues are removed by distilling off the polyamine mixture obtained at 100 mbar and 250 ° C.
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006022448A DE102006022448A1 (de) | 2006-05-13 | 2006-05-13 | Verfahren zur Herstellung von Isocyanaten |
Publications (3)
Publication Number | Publication Date |
---|---|
EP1854783A2 EP1854783A2 (de) | 2007-11-14 |
EP1854783A3 EP1854783A3 (de) | 2009-06-03 |
EP1854783B1 true EP1854783B1 (de) | 2014-11-19 |
Family
ID=38370797
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP07008910.7A Active EP1854783B1 (de) | 2006-05-13 | 2007-05-03 | Verfahren zur Herstellung von Isocyanaten |
Country Status (11)
Country | Link |
---|---|
US (2) | US20070265465A1 (ko) |
EP (1) | EP1854783B1 (ko) |
JP (1) | JP5599129B2 (ko) |
KR (1) | KR101383411B1 (ko) |
CN (1) | CN101302174B (ko) |
BR (1) | BRPI0702581A (ko) |
DE (1) | DE102006022448A1 (ko) |
ES (1) | ES2527718T3 (ko) |
PT (1) | PT1854783E (ko) |
RU (1) | RU2446151C2 (ko) |
TW (1) | TW200808702A (ko) |
Cited By (5)
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WO2017055311A1 (de) | 2015-09-30 | 2017-04-06 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
WO2018041799A1 (de) | 2016-09-01 | 2018-03-08 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
WO2019007834A1 (de) | 2017-07-03 | 2019-01-10 | Covestro Deutschland Ag | Produktionsanlage zur herstellung eines chemischen produkts durch umsetzung h-funktioneller reaktanten mit phosgen und verfahren zum betreiben derselben |
WO2019134909A1 (de) | 2018-01-05 | 2019-07-11 | Covestro Deutschland Ag | Verfahren zur herstellung von methylen-diphenylen-diisocyanaten und polymethylen-polyphenylen-polyisocyanaten |
WO2021122625A1 (de) | 2019-12-18 | 2021-06-24 | Covestro Deutschland Ag | Verfahren zur herstellung von di- und polyisocyanaten der diphenylmethanreihe |
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Publication number | Priority date | Publication date | Assignee | Title |
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DE10260027A1 (de) * | 2002-12-19 | 2004-07-08 | Basf Ag | Verfahren zur Abtrennung und Reinigung von Lösungsmittel von einem Reaktionsgemisch aus einer Isocyanatsynthese |
CA2539243C (en) * | 2003-09-30 | 2010-04-20 | Arthur F. Clark | Method for separating volatile components by dilutive distillation |
DE102008009761A1 (de) | 2008-02-19 | 2009-08-27 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten |
RU2487116C2 (ru) * | 2008-11-26 | 2013-07-10 | Хантсмэн Интернэшнл Ллс | Способ производства изоцианатов |
FR2940283B1 (fr) * | 2008-12-18 | 2011-03-11 | Perstorp Tolonates France | Utilisation d'un reacteur de type piston pour la mise en oeuvre d'un procede de phosgenation. |
WO2010149544A2 (en) * | 2009-06-26 | 2010-12-29 | Basf Se | Process for the production of isocyanates, preferably diisocyanates and polyisocyanates with solvent recirculation |
US20120123153A1 (en) * | 2010-11-17 | 2012-05-17 | Basf Se | Method for purifying mixtures comprising 4,4'-methylenediphenyl diisocyanate |
WO2013139703A1 (de) | 2012-03-19 | 2013-09-26 | Bayer Intellectual Property Gmbh | Verfahren zur herstellung von isocyanaten |
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- 2007-05-14 BR BRPI0702581-5A patent/BRPI0702581A/pt active Search and Examination
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2017055311A1 (de) | 2015-09-30 | 2017-04-06 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
WO2018041799A1 (de) | 2016-09-01 | 2018-03-08 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
WO2019007834A1 (de) | 2017-07-03 | 2019-01-10 | Covestro Deutschland Ag | Produktionsanlage zur herstellung eines chemischen produkts durch umsetzung h-funktioneller reaktanten mit phosgen und verfahren zum betreiben derselben |
WO2019134909A1 (de) | 2018-01-05 | 2019-07-11 | Covestro Deutschland Ag | Verfahren zur herstellung von methylen-diphenylen-diisocyanaten und polymethylen-polyphenylen-polyisocyanaten |
WO2021122625A1 (de) | 2019-12-18 | 2021-06-24 | Covestro Deutschland Ag | Verfahren zur herstellung von di- und polyisocyanaten der diphenylmethanreihe |
Also Published As
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JP2007302672A (ja) | 2007-11-22 |
US20100298596A1 (en) | 2010-11-25 |
BRPI0702581A (pt) | 2008-01-15 |
KR101383411B1 (ko) | 2014-04-08 |
RU2007117488A (ru) | 2008-11-20 |
ES2527718T3 (es) | 2015-01-28 |
JP5599129B2 (ja) | 2014-10-01 |
US20070265465A1 (en) | 2007-11-15 |
KR20070110204A (ko) | 2007-11-16 |
EP1854783A2 (de) | 2007-11-14 |
EP1854783A3 (de) | 2009-06-03 |
RU2446151C2 (ru) | 2012-03-27 |
TW200808702A (en) | 2008-02-16 |
PT1854783E (pt) | 2015-02-04 |
DE102006022448A1 (de) | 2007-11-15 |
CN101302174B (zh) | 2013-10-30 |
CN101302174A (zh) | 2008-11-12 |
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